Work

Synthesis of 2‐Substituted Bicyclo[2.1.1]Hexan‐1‐ols via SmI2‐Mediated Reductive Cyclization Reactions

Year: 2024

Type: article

Abstract: The replacement of benzene rings with saturated bioisosteric counterparts is a key priority in drug discovery programs, and disubstituted bicyclo[2.1.1]hexanes have been recognized as flexible molecular scaffolds that could act as ortho‐substituted benzene bioisosteres. In this study, we outline the synthesis of a wide range of 2‐substituted bicyclo[2.1.1]hexan‐1‐ols, which have the potential to emulate ortho‐phenolic derivatives, via SmI2‐mediated reductive cyclization reactions. The synthetic utility of this methodology was exemplified by the preparation of several saturated analogs of pharmaceutically relevant compounds.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.202400891

Authors: Chih‐Wei Hsu, Chun‐Fu Wu, Yung‐Chi Lee, Woo‐Jin Yoo

Institution: National Taiwan University

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Science and Technology Council, National Taiwan University, National Science and Technology Council

Awards: G5848284922, G8169765665, Synthesis of Non-Rigid Hydrocarbons as Benzene Bioisosteres